In vitro metabolism of chlorotriazines: characterization of simazine, atrazine, and propazine metabolism using liver microsomes from rats treated with various cytochrome P450 inducers

Toxicology and Applied Pharmacology
N HaniokaM Ando

Abstract

The in vitro metabolism of chlorotriazines, simazine (SIZ), atrazine (ATZ), and propazine (PRZ) was studied using control, 3-methylcholanthrene-, phenobarbital-, pyridine-, dexamethasone-, and clofibrate-treated rat liver microsomes. The metabolites were determined by HPLC. The principal reactions by cytochrome P450 (P450) system were N-monodealkylation and isopropylhydroxylation in all rat liver microsomes. As a result, 2-chloro-4-ethylamino-6-amino-1,3,5-triazine (M1) (SIZ-M1 for SIZ and ATZ-M1 for ATZ) and 2-chloro-4-amino-6-isopropylamino-1,3, 5-triazine (M2) (ATZ-M2 for ATZ and PRZ-M2 for PRZ), 2-chloro-4-ethylamino-6-(1-hydroxyisopropylamino)-1,3,5-triazine (M3) (ATZ-M3 for ATZ), and 2-chloro-4-isopropylamino-6-(1-hydroxyisopropylamino)-1,3,5-triazi ne (M4) (PRZ-M4 for PRZ) were detected as the metabolites. N-bidealkylation and 2-hydroxylation were not found in this system. The formation rates of SIZ-M1, ATZ-M1, ATZ-M2, and PRZ-M2 were markedly induced by 3-methylcholanthrene, phenobarbital, and pyridine. On the other hand, the formation rates of ATZ-M3 and PRZ-M4 were significantly induced by phenobarbital, pyridine, and/or clofibrate, but not by 3-methylcholanthrene. The enzyme kinetics of chlorotriazine metabolism were...Continue Reading

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Citations

Jan 18, 2003·Pharmacology & Toxicology·Mette T Skaanild, Christian Friis
Feb 20, 2002·Drug and Chemical Toxicology·Nobumitsu HaniokaMasanori Ando
Jan 19, 2006·Xenobiotica; the Fate of Foreign Compounds in Biological Systems·F HirasawaT Sugiyama
May 8, 2007·Toxicology in Vitro : an International Journal Published in Association with BIBRA·María Elena Calderón-SeguraJosé Sánchez-Rincón
Dec 26, 2006·Toxicology in Vitro : an International Journal Published in Association with BIBRA·Tami S McMullinWilliam H Hanneman
Dec 5, 2013·Journal of Zhejiang University. Science. B·Robinson David Jebakumar SolomonVelayudhan Satheeja Santhi
Sep 9, 2017·Xenobiotica; the Fate of Foreign Compounds in Biological Systems·Arthur D ZimmermanChad D Foradori
Jun 22, 2006·Archives of Environmental Contamination and Toxicology·M B MurphyJ P Giesy
Jun 30, 2006·Toxicological Sciences : an Official Journal of the Society of Toxicology·J Thomas Sanderson
Feb 9, 2010·Toxicology Mechanisms and Methods·Mohan SinghRavi Kiran
Mar 29, 2001·Journal of Pharmaceutical and Biomedical Analysis·N HaniokaM Ando
Nov 1, 2011·Ecotoxicology and Environmental Safety·J VelisekZ Svobodova
Feb 9, 2010·Experimental and Toxicologic Pathology : Official Journal of the Gesellschaft Für Toxikologische Pathologie·Mohan SinghRavi Kiran

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